On Tuesday, documents filed with the U.S. Bankruptcy Court in the District of Delaware showed that FriendFinder Networks (FFNT[3]) has debts of between $500 million and $1 billion compared to assets of less than $10 million. FriendFinder operates a number of “adult” websites and publishes Penthouse magazine, Reuters notes.

The company, which launched a failed $210 million bid to buy rival Playboy in 2010, generated revenue of $293.70 million over the past year, but hasn’t actually made money since 2008.

FriendFinder has defaulted on some loan payments. It is looking to restructure its debt and has reached agreements with some of its lenders.

Not surprisingly, FriendFinder’s shares plunged more than 80% in over-the-counter trading on Tuesday.

The bankruptcy filing is the latest bit of bad news for the porn industry. Earlier this month, the filming of pornographic movies in California was halted after several performers tested positive for HIV infection[4].